Compounds and methods of arylmethylation (benzylation) as protection for alcohol groups during chemical synthesis

Abstract

A process for benzylating an alcohol includes mixing 2-benzyloxy-1-methylpyridinium triflate in an aromatic hydrocarbon solvent having a predetermined boiling point; adding an acid scavenger to the mixture; combining the alcohol to be benzylated with the mixture; reacting the alcohol with the 2-benzyloxy-1-methylpyridinium triflate by heating above ambient temperature to generate the benzylated alcohol; and separating the benzylated alcohol from the mixture.

1. A method of making 2-benzyloxy-1-methylpyridinium triflate, the method comprising:
 adding methyl trifluoromethanesulfonate to a cold solution of 2-benzyloxypyridine in toluene; and 
 reacting the solution at ambient temperature to generate a precipitate of 2-benzyloxy-1-methylpyridinium triflate. 
 
     
     
       2. A method of synthesizing 2-benzyloxy-1-methylpyridinium triflate, the method comprising reacting methyl trifluoromethanesulfonate with 2-benzyloxypyridine in toluene to generate a precipitate of 2-benzyloxy-1-methylpyridinium triflate. 
     
     
       3. The method of  claim 1  further comprising separating the precipitate and drying the separated precipitate. 
     
     
       4. The compound 2-benzyloxy-1-methylpyridinium triflate made according to the method of  claim 1 . 
     
     
       5. The compound 2-benzyloxy-1-methylpyridinium triflate made according to the method of  claim 2 . 
     
     
       6. A compound having the formula 
       
         
           
           
               
               
           
         
       
       wherein Me comprises a methyl group, Bn comprises a benzyl group and Tf comprises a trifluoro group.